Hydrochloric Acid → HCID 86287692, compound

HRID 633524Notes

Reaction equation

[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:20]3[C:15](=[C:16]([O:21]C)[N:17]=[CH:18][CH:19]=3)[N:14]([CH3:23])[CH:13]=2)=[CH:7][C:6]=1[NH:24][S:25]([CH3:28])(=[O:27])=[O:26].Cl.O1CCOCC1>>[F:1][C:2]1[CH:32]=[C:31]([F:33])[CH:30]=[CH:29][C:3]=1[O:4][C:5]1[CH:10]=[C:9]([F:11])[C:8]([C:12]2[C:20]3[CH:19]=[CH:18][NH:17][C:16](=[O:21])[C:15]=3[N:14]([CH3:23])[CH:13]=2)=[CH:7][C:6]=1[NH:24][S:25]([CH3:28])(=[O:27])=[O:26]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 312751,4-Dioxane

HCID 90418106HCID 90418106, compound

Product 1

HCID 86287692HCID 86287692, compoundYield 34.4%

Conditions

Temperature: 70 °C

Procedure

The product from Example 12A (0.066 g, 0.138 mmol) and 4 M hydrogen chloride in dioxane (10 mL, 40.0 mmol) were combined and heated at 70° C. for 24 hours, cooled and concentrated. The residue was purified by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%) to afford the title compound (0.022 g, 34%). 1H NMR (300 MHz, DMSO-d6) δ ppm 11.00 (d, J=5.09 Hz, 1H) 9.53 (s, 1H) 7.47-7.59 (m, 3H) 7.30-7.41 (m, 1H) 7.11-7.20 (m, 1H) 6.90-6.96 (m, 1H) 6.78 (d, J=10.85 Hz, 1H) 6.49 (d, J=7.12 Hz, 1H) 4.11 (s, 3H) 3.05 (s, 3H). MS (ESI+) m/z 464 (M+H)+.

Workup

temperaturecooled
concentrationconcentrated
customThe residue was purified by reverse phase HPLC (C18, CH3CN/water (0.1% TFA), 10-100%)

Sources & evidence

ORD record: ord-ebbd0253afb4489bacc7620f6e62d8bb
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321764B2

Reaction notes

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